EP1013699A2 - Polyorganosiloxane mit mindestens einer organofunktionellen Gruppe welche mehrfach hydrolysierbare Gruppen aufweist - Google Patents

Polyorganosiloxane mit mindestens einer organofunktionellen Gruppe welche mehrfach hydrolysierbare Gruppen aufweist Download PDF

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Publication number
EP1013699A2
EP1013699A2 EP99310235A EP99310235A EP1013699A2 EP 1013699 A2 EP1013699 A2 EP 1013699A2 EP 99310235 A EP99310235 A EP 99310235A EP 99310235 A EP99310235 A EP 99310235A EP 1013699 A2 EP1013699 A2 EP 1013699A2
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Prior art keywords
polyorganosiloxane
integer
formula
carbon atoms
radical
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EP99310235A
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English (en)
French (fr)
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EP1013699A3 (de
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Robert Harold Krahnke
Thimothy B. Lueder
Richard Alan Palmer
Nick Evan Shephard
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Dow Silicones Corp
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Dow Corning Corp
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    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
    • C08G77/00—Macromolecular compounds obtained by reactions forming a linkage containing silicon with or without sulfur, nitrogen, oxygen or carbon in the main chain of the macromolecule
    • C08G77/04—Polysiloxanes
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
    • C08G77/00—Macromolecular compounds obtained by reactions forming a linkage containing silicon with or without sulfur, nitrogen, oxygen or carbon in the main chain of the macromolecule
    • C08G77/48—Macromolecular compounds obtained by reactions forming a linkage containing silicon with or without sulfur, nitrogen, oxygen or carbon in the main chain of the macromolecule in which at least two but not all the silicon atoms are connected by linkages other than oxygen atoms
    • C08G77/50—Macromolecular compounds obtained by reactions forming a linkage containing silicon with or without sulfur, nitrogen, oxygen or carbon in the main chain of the macromolecule in which at least two but not all the silicon atoms are connected by linkages other than oxygen atoms by carbon linkages

Definitions

  • This invention relates to a polyorganosiloxane comprising at least one organofunctional group per molecule having multiple hydrolyzable groups.
  • compositions which cure to elastomeric materials at room temperature are well known.
  • Such compositions can be obtained by mixing polydiorganosiloxanes having reactive or hydrolyzable groups, such as silanol or alkoxy groups, with silane crosslinking agents, for example, alkoxysilanes, acetoxysilanes, oximosilanes or aminosilanes and catalysts as needed.
  • silane crosslinking agents for example, alkoxysilanes, acetoxysilanes, oximosilanes or aminosilanes and catalysts as needed.
  • the polydiorganosiloxanes have 1 to 3 reactive groups per chain end. Compositions comprising these ingredients can then be cured by exposure to atmospheric moisture at room temperature.
  • the cure rate of a particular composition is dependent on a number of factors including the type of reactive or hydrolyzable group utilized. It is known that different hydrolyzable groups have different reactivities and even the same type of hydrolyzable group can have different reactivities. For example, in the presence of moisture, a silicon-bonded acetoxy group will hydrolyze more rapidly than a silicon-bonded alkoxy group.
  • each silicon-bonded alkoxy group has a different reactivity, with the alkoxy group first reacted being "most reactive.”
  • the first alkoxy group on a silicon atom reacts it takes a longer time for the second alkoxy group on the same silicon atom to react, and even longer for the third. Therefore, it would be desirable to prepare polyorganosiloxanes comprising at least one organofunctional group per molecule having more than one "most" reactive hydrolyzable group.
  • the objective of the present invention is to prepare a polyorganosiloxane comprising at least one organofunctional group per molecule having multiple hydrolyzable groups.
  • the present invention is a polyorganosiloxane comprising at least one organofunctional group per molecule having multiple hydrolyzable groups.
  • the organofunctional group is described by the formula -Z b -R 4 (Z-SiR 2 n X 3-n ) a where each R 2 is independently selected from a hydrogen atom and monovalent hydrocarbon radicals having 1 to 18 carbon atoms; each Z is independently selected from divalent hydrocarbon radicals having 2 to 18 carbon atoms or a combination of divalent hydrocarbon radicals and siloxane segments; R 4 is independently selected from a silicon atom or a siloxane radical comprising at least two silicon atoms and each Z is bonded to a silicon atom of R 4 with the remaining valences of the silicon atoms of R 4 being bonded to a hydrogen atom, a monovalent hydrocarbon radical having 1 to 18 carbon atoms or forming siloxane bonds; each X is independently selected from halogen, alkoxy, acyloxy or ketox
  • the present invention is a polyorganosiloxane comprising at least one organofunctional group described by the formula -Z b -R 4 (Z-SiR 2 n X 3-n ) a (I) where each R 2 is independently selected from a hydrogen atom and monovalent hydrocarbon radicals having 1 to 18 carbon atoms; each Z is independently selected from divalent hydrocarbon radicals having 2 to 18 carbon atoms or a combination of divalent hydrocarbon radicals and siloxane segments described by the formula where R 2 is as defined above; each G is an independently selected divalent hydrocarbon radical having 2 to 18 carbon atoms; and c is a whole number from 1 to 6; R 4 is independently selected from a silicon atom or a siloxane radical comprising at least two silicon atoms and each Z is bonded to a silicon atom of R 4 with the remaining valences of the silicon atoms of R 4 being bonded to a hydrogen atom, a monovalent hydrocarbon radical having 1 to 18 carbon atoms or forming
  • a first embodiment are those polyorganosiloxanes comprising repeating siloxy units described by the formula -(R 3 2 SiO) h - where each R 3 is independently selected from a hydrogen atom, monovalent hydrocarbon radicals having 1 to 18 carbon atoms and organofunctional group described by -Z b -R 4 (Z-SiR 2 n x 3-n ) a and h is a value such that the polyorganosiloxane has a viscosity within a range of 0.5 to 3000 Pa.s at 25°C., each R 2 is independently selected from a hydrogen atom or monovalent hydrocarbon radicals having 1 to 18 carbon atom; each Z is independently selected from divalent hydrocarbon radicals having 2 to 18 carbon atoms or a combination of divalent hydrocarbon radicals and siloxane segments described by the formula where R 2 is defined above; each G is an independently selected divalent hydrocarbon radical having 2 to 18 carbon atoms; c is a whole number from 1 to 6; R 4 is independently
  • a second embodiment are those polyorganosiloxanes defined above in the first embodiment except each R 3 is selected from alkyl radicals having from 1 to 8 carbon atoms, at least 95 mole percent of R 3 are alkyl radicals and h is a value such that the polyorgano-siloxane has a viscosity within a range of 5 to 200 Pa ⁇ s at 25°C.
  • a third embodiment are those polyorganosiloxanes defined above in the first embodiment except the organofunctional group is selected from or where m is an integer from 2 to 7; p is an integer from 0 to 6; m+p is an integerfrom 2 to 8; t is 2 or 3; u is an integer from 0 to 5; and v is an integer from 0 to 5.
  • One group of polyorganosiloxanes of this embodiment which are preferred are those in which the organofunctional group has formula (III) where each R 2 is an independently selected alkyl radical having 1 to 8 carbon atoms, X is alkoxy and t is 2.
  • each R 2 is an independently selected alkyl radical having 1 to 8 carbon atoms
  • X is alkoxy
  • m is an integer from 2 to 4
  • p is an integer of 0 to 3
  • m+p is an integer from 2 to 5.
  • a fourth embodiment are those polyorganosiloxanes comprising repeating siloxy units described by the formula -(R 3 2 SiO) h - where each R 3 is independently selected from a hydrogen atom, monovalent hydrocarbon radicals having 1 to 18 carbon atoms and organofunctional group described by -Z b -R 4 (Z-SiR 2 n x 3-n ) a and h is a value such that the polyorganosiloxane has a viscosity within a range of 0.5 to 3000 Pa ⁇ s at 25°C., each R 2 is independently selected from a hydrogen atom or monovalent hydrocarbon radicals having 1 to 18 carbon atom; Z is a divalent hydrocarbon radicals having 2 to 18 carbon atoms; R 4 is independently selected from a silicon atom or a siloxane radical having at least two silicon atoms and each Z is bonded to a silicon atom of R 4 with the remaining valences of the silicon atoms of R 4 being bonded to a hydrogen
  • a fifth embodiment are those polyorganosiloxanes in which the chain ends are each selected from -OSiR 1 3 , -OSiR 1 2 OH, -OSiR 1 2 H, -OSiR 1 n x 3-n , -ZSiR 2 n x 3-n or -Z b -R 4 (Z-SiR 2 n x 3-n ) a where each R 1 and R 2 is an independently selected hydrocarbon radical having 1 to 8 carbon atoms; Z is alkylene; X is alkoxy; a is at least 2; b is 0 or 1; provided, when b is 0, R 4 is bonded to the polyorgano-siloxane through a siloxane bond, R 4 is independently selected from a silicon atome or a siloxane radical having at least two silicon atoms and each Z is bonded to a silicon atom of R 4 with the remaining valences of the silicon atoms of R 4 being bonded to a hydrogen atom
  • a sixth embodiment are those polyorganosiloxanes comprising repeating siloxy units described by the formula -(R 3 2 SiO) h - where each R 3 is independently selected from a hydrogen atom, monovalent hydrocarbon radicals having 1 to 18 carbon atoms and organofunctional group described by -Z b -R 4 (Z-SiR 2 n x 3-n ) a and h is a value such that the polyorganosiloxane has a viscosity within a range of 0.5 to 3000 Pa ⁇ s at 25°C., each R 2 is independently selected from a hydrogen atom or monovalent hydrocarbon radicals having 1 to 18 carbon atom; each Z is independently selected from divalent hydrocarbon radicals having 2 to 18 carbon atoms or a combination of divalent hydrocarbon radicals and siloxane segments described by the formula where R 2 is defined above; each G is an independently selected divalent hydrocarbon radical having 2 to 18 carbon atoms; c is a whole number from 1 to 6; each X is
  • the polyorganosiloxane of the present invention comprises at least one organofunctional group described by formula (I).
  • the polyorganosiloxane may be linear or branched and may be a homopolymer, copolymer or terpolymer.
  • the polyorganosiloxane may be a single species or a mixture of different polymers.
  • the repeating units of the polyorganosiloxane includes siloxy units such as described by formula R 3 s SiO (4-s)/2 where s is 0, 1 or 2 and each R 3 is independently selected from a hydrogen atom, monovalent hydrocarbon radicals having 1 to 18 carbon atoms and the organofunctional group described by formula (I), ie, -Z b -R 4 (Z-SiR 2 n x 3-n ) a , where Z, R 4 , R 2 , X, n, a and b are as defined above.
  • Each R 2 of the organofunctional group described by formula (I) is independently selected from a hydrogen atom or monovalent hydrocarbon radicals having 1 to 18 carbon atoms.
  • the monovalent hydrocarbon radicals represented by R 2 may be substituted or unsubstituted.
  • Examples of monovalent hydrocarbon radicals represented by R 2 include alkyl radicals such as methyl, ethyl, hexyl, 3,3,3-trifluoropropyl, chloromethyl and octadecyl; alkenyl radicals such as vinyl, allyl and butadienyl; cycloalkyl radicals such as cyclobutyl, cyclopentyl and cyclohexyl; cycloalkenyl radicals such as cyclopentenyl and cyclohexenyl; aryl radicals such as phenyl and xylyl; aralkyl radicals such as benzyl; and alkaryl radicals such as tolyl.
  • Each X of the organofunctional group described by formula (I) is independently selected from halogen, alkoxy, acyloxy or ketoximo.
  • the halogen atoms can be chlorine, bromine, fluorine or iodine.
  • alkoxy groups include methoxy, ethoxy; iso-propoxy, butoxy, cyclohexoxy, phenoxy, 2-chloroethoxy, 3,3,3-trifluoropropoxy, 2-methoxyethoxy and p-methoxyphenoxy.
  • alkoxy groups include methoxy, ethoxy; iso-propoxy, butoxy, cyclohexoxy, phenoxy, 2-chloroethoxy, 3,3,3-trifluoropropoxy, 2-methoxyethoxy and p-methoxyphenoxy.
  • acyloxy groups include acetoxy, propionoxy, benzoyloxy and cyclohexoyloxy.
  • ketoximo groups include dimethylketoximo, methylethylketoximo, methylpropylketoximo, methylbutylketoximo and diethylketoximo.
  • each X is independently selected from alkoxy, acyloxy and ketoximo. More preferably each X is independently selected from alkoxy or acyloxy with each X being an independently selected alkoxy group being most preferred.
  • Each Z of the organofunctional group described by formula (I) is selected from divalent hydrocarbon radicals having 2 to 18 carbon atoms or a combination of divalent hydrocarbon radicals and siloxane segments described by formula where R 2 is as defined above; each G is an independently selected divalent hydrocarbon radical having 2 to 18 carbon atoms; and c is a whole number from 1 to 6.
  • the divalent hydrocarbon radicals represented by Z and G may be substituted or unsubstituted.
  • Examples of the divalent hydrocarbon radicals having 2 to 18 carbon atoms represented by Z and G include alkylene radicals such as ethylene, methylmethylene, propylene, butylene, pentylene, hexylene, 3,3,3-trifluoropropylene and chloromethylene and octadecylene; alkenylene radicals such as vinylene, allylene and butadienylene; cycloalkylene radicals such as cyclobutylene, cyclopentylene and cyclohexylene; cycloalkenylene radicals such as cyclopentenylene and cyclohexenylene; arylene radicals such as phenylene and xylylene; aralkylene radicals as benzylene; and alkarylene radicals such as tolylene.
  • each G is preferably an alkylene radical and each G is more preferably an alkylene radical having 2 to 8 carbon atoms.
  • Z is a divalent hydrocarbon radical having 2 to 18 carbon atoms. It is more preferred for Z to be an alkylene radical, with an alkylene radical having 2 to 8 carbon atoms being most preferred.
  • n of the organofunctional group described by formula (I) is 0, 1 or 2 and is preferably 0 or 1.
  • Subscript a of the organofunctional group described by formula (I) is at least 2 and is preferably from 2 to 8.
  • Subscript b of the organofunctional group described by formula (I) is 0 or 1, provided, when b is 0, R 4 is bonded to the polyorganosiloxane through a siloxane bond.
  • R 4 of the organofunctional group described by formula (I) is selected from a silicon atom or a siloxane radical comprising at least two silicon atoms and each Z group is bonded to a silicon atom of R 4 with the remaining valences of the silicon atoms of R 4 being bonded to a hydrogen atom, a monovalent hydrocarbon radical having 1 to 18 carbon atoms or forming siloxane bonds.
  • the siloxane radical represented by R 4 may have a linear, branched, resinous or cyclic structure.
  • R 4 is selected from a silicon atom or a siloxane radical comprising at least two silicon atoms described by formula (R 2 3 SiO 1/2 ) d (R 2 2 SiO 2/2 ) e (R 2 SiO 3/2 ) f (SiO 4/2 ) g where R 2 is as defined above and the sum of d+e+f+g is in a range from 2 to 50, provided that at least two R 2 groups are replaced by Z groups of the organofunctional group as described by formula (I), ie, -Z b -R 4 (Z-SiR 2 n x 3-n ) a , where Z, R 4 , R 2 , X, n, a and b are as defined above, since it is required that each Z group is bonded to a silicon atom of R 4 .
  • R 4 is selected from a silicon atom or a siloxane radical comprising at least two silicon atoms described by formula (II) where d is an integer from 0 to 5, e is an integer from 0 to 30, f is an integer from 0 to 5, g is an integer from 0 to 5, the sum of d+e+f+g is greater than 2, and provided that at'least 2 R 2 groups are replaced by Z groups of the organofunctional group as described by formula (I).
  • each R 3 of the siloxy unit of the polyorganosiloxane may also be a hydrogen atom or a monovalent hydrocarbon radical having 1 to 18 carbon atoms.
  • the hydrocarbon radicals represented by R 3 may be substituted or unsubstituted. Examples of monovalent hydrocarbon radicals having 1 to 18 carbon atoms include those described above for R 2 .
  • each R 3 is independently selected from a hydrogen atom, monovalent hydrocarbon radicals having 1 to 8 carbon atoms or the organofunctional group described by formula (I), ie, -Z b -R 4 (Z-SiR 2 n X 3-n ) a , where Z, R 4 , R 2 , X, n, a and b are as defined above. More preferably each R 3 is independently selected from alkyl radicals or the organofunctional group described by formula (I).
  • the preferred polyorganosiloxane comprises repeating siloxy units described by the formula -(R 3 2 SiO) h -, where R 3 is as described above and at least 80 mole percent of R 3 are hydrocarbon radicals and h is a value such that the polyorganosiloxane has a viscosity within a range of 0.5 to 3000 Pa ⁇ s at 25°C.
  • R 3 in the more preferred polyorganosiloxane comprises at least 95 mole percent hydrocarbon radicals. Most preferably, substantially all the R 3 's are hydrocarbon radicals and h is within a range of 5 to 200 Pa ⁇ s at 25°C.
  • the polyorganosiloxane is required to have at least one organofunctional group described by formula (I), ie, -Z b -R 4 (Z-SiR 2 n x 3-n ) a , where R 2 , R 4 , X, Z, n, a and b are as defined above.
  • the organofunctional group can be bonded in a pendant position on the polyorganosiloxane chain or at the polyorganosiloxane chain end or in the case where more than one organofunctional group is bonded to the polyorgano-siloxane both pendant and terminal positions.
  • the organofunctional group is bonded at the polyorganosiloxane chain end. If greater than one organofunctional group is bonded to the polyorganosiloxane, it is preferable that each organofunctional group be separated by at least 200 repeating siloxy units.
  • organofunctional groups can be bonded at various points on the polyorganosiloxane not just at the chain end, other types of groups may also be found at the polyorganosiloxane's chain end.
  • useful groups include -OSiR 1 3 , -OSiR 1 2 OH, -OSiR 1 2 H, -OSiR 1 n x 3-n and -ZSiR 2 n X 3-n ; where R 2 , X, Z and n are as described above and each R 1 is an independently selected hydrocarbon radical having 1 to 18 hydrocarbon radicals. Examples of monovalent hydrocarbon radicals having 1 to about 18 carbon atoms are as described above for R 2 .
  • R 1 is a monovalent hydrocarbon radical having 1 to 8 carbon atoms with a monovalent hydrocarbon radical having 1 to 4 carbon atoms being most preferred.
  • chain end groups other than the organofunctional group described by formula (I) include -OSiMe 3 , -OSiEt 3 , -OSiViMe 2 , -OSiMeViPh, -OSi(Me 2 )OH, -OSi(Me 2 )H, -OSi(Me 2 )OH, -OSi(OMe) 3 and -CH 2 CH 2 Si(OMe) 3 , where Me is methyl, Vi is vinyl and Ph is phenyl.
  • organofunctional groups useful in the present invention are selected from or where R 2 , X, Z and n are as described above.
  • subscript u is an integer from 0 to 5.
  • subscript u is an integer from 0 to 1.
  • subscript v is an integer from 0 to 5.
  • subscript v is an integer from 0 to 1.
  • subscript m is an integer from 2 to 7.
  • subscript m is an integer from 2 to 4.
  • subscript p is an integer from 0 to 6.
  • subscript p is an integer from 0 to 3.
  • m+p is a whole number from 2 to 8.
  • m+p is a whole number from 2 to 5.
  • the polyorganosiloxanes comprising at least one organofunctional group described by formula (I) may be prepared, for example, by mixing at least one organofunctional siloxane selected from or with a polyorganosiloxane comprising at least one silicon-bonded hydrogen atom or a group comprising at least one aliphatic unsaturation in the presence of a hydrosilylation catalyst, where R 2 , X, Z, m, n, p, t, u and v are as defined above and Y is independently selected from hydrogen, hydrocarbon radicals having one aliphatic unsaturation and 2 to 18 carbon atoms or a combination of hydrocarbon radicals and siloxane segments described by formula where R 2 , G and c are as defined above and M is selected from hydrocarbon radicals having one aliphatic unsaturation and 2 to 18 carbon atoms.
  • the hydrocarbon radicals of Y and M may be substituted or unsubstituted.
  • Examples of the hydrocarbon radicals having one aliphatic unsaturation of Y and M include alkenyl radicals such as vinyl, allyl, butenyl, hexenyl and octenyl, and cycloalkenyl radicals such as cyclopentenyl, cyclohexenyl and chlorocyclopentenyl.
  • alkenyl radicals such as vinyl, allyl, butenyl, hexenyl and octenyl
  • cycloalkenyl radicals such as cyclopentenyl, cyclohexenyl and chlorocyclopentenyl.
  • G be an alkylene radical and M an alkenyl radical, and more preferable that G be an alkylene radical having 2 to 8 carbon atoms and M an alkenyl radical having 2 to 8 carbon atoms.
  • Y is selected from hydrogen or a hydrocarbon radical having one aliphatic unsaturation. More preferably, Y is selected from hydrogen or an alkenyl radical, with hydrogen and an alkenyl radical having 2 to 8 carbon atoms being most preferred.
  • the polyorganosiloxane when Y of the organofunctional group is hydrogen then the polyorganosiloxane must contain at least one aliphatic unsaturation, and similarly when Y of the organofunctional group is a group having one aliphatic unsaturation then the polyorganosiloxane must contain at least one silicon-bonded hydrogen atom.
  • the organofunctional siloxanes described by formulas (V) and (VI) may be prepared by known methods such as taught in Krahnke et al. "An Organosilicon Endcapper Having One Silicon-Bonded Hydrogen Atom," U.S. Application No. 09/218,534 filed December 21, 1998; Krahnke et al. "A Cyclic Organosilicon Endcapper Having One Silicon-Bonded Hydrogen Atom," U.S. Application No. 09/218,536 filed December 21, 1998; Krahnke et al. "An Organosilicon Endcapper Having One Aliphatic Unsaturation," U.S. Application No. 09/218,365 filed December 21, 1998; and Krahnke et al.
  • the polyorganosiloxane having at least one silicon-bonded hydrogen atom or at least one aliphatic unsaturation may be prepared by known methods.
  • Catalysts typically employed for hydrosilylation reactions such as platinum group metal-containing catalysts are used as catalysts for the reaction between the organofunctional siloxanes described by Formulas (V) and (VI) and the polyorganosiloxane comprising at least one silicon-bonded hydrogen or at least one group comprising one aliphatic unsaturation.
  • platinum group metal it is meant ruthenium, rhodium, palladium, osmium, iridium and platinum.
  • Platinum group metal-containing catalysts particularly useful in the present composition are the platinum complexes prepared as described by U.S. Patents 3,419,593 and 5,175,325.
  • Preferred catalysts are complexes of platinum with vinylsiloxane.
  • the amount of catalyst useful in effecting the hydrosilylation reaction to make the composition of the present invention is not narrowly limited as long as there is an amount present to accelerate a reaction between the hydrosilyl groups and the groups comprising one aliphatic unsaturation.
  • the appropriate amount of the catalyst will depend upon the particular catalyst used. In general as low as 0.1 part by weight of platinum group metal based on 1 million parts by weight of total reactants may be useful (ie, 0.1 ppm).
  • the amount of platinum group metal is from 0.5 to 10 ppm. More preferred is from 1 to 5 ppm platinum group metal.
  • the platinum group metal-containing catalyst may be added as a single species or as a mixture of two or more different species. Adding the catalyst as a single species is preferred.
  • the temperature of the hydrosilylation reaction is not strictly specified, but usually falls within the range of 20° to 150°C. and preferably within the range of 30° to 110°C.
  • the molar ratio of reactive sites on the polyorganosiloxane relative to the reactive sites on the organofunctional siloxane needed to prepare the polyorganosiloxane of the present invention will be determined by the amount of organofunctional groups desired on the polyorganosiloxane but amounts must be used so that each polyorganosiloxane molecule comprises at least one organofunctional group.
  • a preferable ratio is 1:1 to 1.5:1.
  • reactive sites means either aliphatic unsaturated groups or silicon-bonded hydrogen groups, each type can be on either the polyorganosiloxane or organofunctional siloxane but one type must be on each of them.
  • the polyorganosiloxanes comprising at least one organofunctional group per molecule described by formula (I) are useful in the preparation of sealants, adhesives and coatings.

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EP99310235A 1998-12-21 1999-12-20 Polyorganosiloxane mit mindestens einer organofunktionellen Gruppe welche mehrfach hydrolysierbare Gruppen aufweist Withdrawn EP1013699A3 (de)

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US217477 1998-12-21
US09/217,477 US6127502A (en) 1998-12-21 1998-12-21 Polyorganosiloxanes having at least one organofunctional group with multiple hydrolyzable groups

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EP1013699A2 true EP1013699A2 (de) 2000-06-28
EP1013699A3 EP1013699A3 (de) 2001-05-16

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JP (1) JP2000186147A (de)
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